Tiptree (TIPT)
Market Price (12/4/2025): $18.49 | Market Cap: $694.6 MilSector: Financials | Industry: Life & Health Insurance
Tiptree (TIPT)
Market Price (12/4/2025): $18.49Market Cap: $694.6 MilSector: FinancialsIndustry: Life & Health Insurance
Investment Highlights
Why It Matters
Which of these 2 stories sounds closer for this stock?
1. Generates cash flow
The stock generated 4% or more of the share price (called cash flow yield), and shows moderate 10-15% or more growth.
2. Riding a trend
Think Tesla during the pandemic of 2020 when EVs were riding a cultural high, or Nvidia in the current AI boom, or even Figma. These companies don’t have enough yield, or, enough growth, or both - however - they are riding a trend. They have momentum. These can be more volatile - they don’t have the floor of strong cash flow
| Attractive yieldTotal YieldTotal Yield = Earnings Yield + Dividend Yield, Earnings Yield = Net Income / Market Cap Dividend Yield = Total Dividends / Market Cap is 10%, Dividend Yield is 3.4%, ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is 6.3%, FCF Yield is 26% | Weak multi-year price returns2Y Excs Rtn is -47%, 3Y Excs Rtn is -28% | |
| Cash is significant % of market capNet D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is -14% | ||
| Low stock price volatilityVol 12M is 41% | ||
| Megatrend and thematic driversMegatrends include AI in Financial Services, and Fintech & Digital Payments. Themes include AI for Fraud Detection, and Specialty Insurance Platforms. |
| Attractive yieldTotal YieldTotal Yield = Earnings Yield + Dividend Yield, Earnings Yield = Net Income / Market Cap Dividend Yield = Total Dividends / Market Cap is 10%, Dividend Yield is 3.4%, ERPEquity Risk Premium (ERP) = Total Yield - Risk Free Rate, Reflects the premium above risk free assets offered by the investment. is 6.3%, FCF Yield is 26% |
| Cash is significant % of market capNet D/ENet Debt/Equity. Debt net of cash. Negative indicates net cash. Equity is taken as the Market Capitalization is -14% |
| Low stock price volatilityVol 12M is 41% |
| Megatrend and thematic driversMegatrends include AI in Financial Services, and Fintech & Digital Payments. Themes include AI for Fraud Detection, and Specialty Insurance Platforms. |
| Weak multi-year price returns2Y Excs Rtn is -47%, 3Y Excs Rtn is -28% |
Valuation, Metrics & Events
TIPT Stock
Why The Stock Moved
Qualitative Assessment
AI Generated Analysis | Feedback
Here are five key points explaining the approximate -20.3% stock movement for Tiptree (TIPT) between August 31, 2025, and December 4, 2025:
1. Shareholder opposition to the Fortegra merger deal. Investment firm Veradace Partners, holding a 5.1% stake in Tiptree, actively urged shareholders to vote against the proposed sale of its subsidiary, The Fortegra Group, to DB Insurance Co., Ltd., citing concerns that the transaction was undervalued, resulted from a rushed process, and benefited Tiptree management more than shareholders. This opposition likely contributed to market uncertainty and negative sentiment surrounding the deal.
2. Approval of the Fortegra merger despite opposition. On December 3, 2025, Tiptree shareholders approved the acquisition of The Fortegra Group, Inc. by DB Insurance Co., Ltd.. While the merger was approved, the significant shareholder opposition, particularly regarding the perceived undervaluation of Fortegra, may have continued to weigh on the stock, contributing to the broader decline observed in the period. InvestingPro data indicated an approximately 18% decline in Tiptree's stock price over the six months leading up to December 3, 2025.
Stock Movement Drivers
Return vs. Risk
Price Returns Compared
| 2020 | 2021 | 2022 | 2023 | 2024 | 2025 | Total [1] | |
|---|---|---|---|---|---|---|---|
| Returns | |||||||
| TIPT Return | -37% | 180% | 1% | 39% | 13% | -10% | 154% |
| Peers Return | -7% | 26% | 8% | 11% | 24% | 3% | 80% |
| S&P 500 Return | 16% | 27% | -19% | 24% | 23% | 16% | 112% |
Monthly Win Rates [3] | |||||||
| TIPT Win Rate | 33% | 67% | 50% | 50% | 42% | 40% | |
| Peers Win Rate | 42% | 55% | 45% | 48% | 52% | 60% | |
| S&P 500 Win Rate | 58% | 75% | 42% | 67% | 75% | 70% | |
Max Drawdowns [4] | |||||||
| TIPT Max Drawdown | -45% | -3% | -28% | -10% | -18% | -17% | |
| Peers Max Drawdown | -44% | -2% | -10% | -13% | -3% | -10% | |
| S&P 500 Max Drawdown | -31% | -1% | -25% | -1% | -2% | -15% | |
[1] Cumulative total returns since the beginning of 2020
[2] Peers: OSG, MFC, AFL, MET, PRU. See TIPT Returns vs. Peers.
[3] Win Rate = % of calendar months in which monthly returns were positive
[4] Max drawdown represents maximum peak-to-trough decline within a year
[5] 2025 data is for the year up to 12/3/2025 (YTD)
How Low Can It Go
| Event | TIPT | S&P 500 |
|---|---|---|
| 2022 Inflation Shock | ||
| % Loss | -42.6% | -25.4% |
| % Gain to Breakeven | 74.1% | 34.1% |
| Time to Breakeven | 98 days | 464 days |
| 2020 Covid Pandemic | ||
| % Loss | -44.6% | -33.9% |
| % Gain to Breakeven | 80.5% | 51.3% |
| Time to Breakeven | 364 days | 148 days |
| 2018 Correction | ||
| % Loss | -32.6% | -19.8% |
| % Gain to Breakeven | 48.4% | 24.7% |
| Time to Breakeven | 263 days | 120 days |
Compare to OSG, MFC, AFL, MET, PRU
In The Past
Tiptree's stock fell -42.6% during the 2022 Inflation Shock from a high on 4/23/2021. A -42.6% loss requires a 74.1% gain to breakeven.
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Asset Allocation
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Latest Trefis Analyses
| Title | Topic | |
|---|---|---|
| DASHBOARDS | ||
| Tiptree vs. S&P500 Correlation | Correlation | |
| Tiptree Price Volatility | Volatility | |
| Tiptree Financial (TIPT) Stock Has 54% Chance Of Rise In The Next One Month | ||
| Dates Cached For TIPT | ||
| Tiptree Financial (TIPT) Stock Has 61% Chance Of Rise In The Next One Month | ||
| Tiptree vs. Small Cap Stocks: Which Is A Better Investment? | Investment Theme Comparisons | |
| Tiptree vs. Inflation Stocks: Which Is A Better Investment? | Investment Theme Comparisons | |
| Tiptree vs. Fintech Stocks: Which Is A Better Investment? | Investment Theme Comparisons | |
| Tiptree Trading Strategy: Does Buying The Stock When EPS Growth Accelerates Make Sense? | Technicals | |
| How Quickly Has Tiptree Shown Bullish Reversal Historically? | Technicals |
| Title | |
|---|---|
| ARTICLES |
Trade Ideas
Select past ideas related to TIPT. For more, see Trefis Trade Ideas.
| Date | Ticker | Company | Category | Trade Strategy | 6M Fwd Rtn | 12M Fwd Rtn | 12M Max DD |
|---|---|---|---|---|---|---|---|
| 11212025 | WU | Western Union | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | 7.5% | 7.5% | -0.4% |
| 11212025 | COIN | Coinbase Global | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 15.2% | 15.2% | 0.0% |
| 11142025 | PYPL | PayPal | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | -2.5% | -2.5% | -7.5% |
| 11142025 | V | Visa | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | -0.1% | -0.1% | -2.7% |
| 11072025 | WD | Walker & Dunlop | Dip Buy | DB | P/E OPMDip Buy with Low PE and High MarginBuying dips for companies with tame PE and meaningfully high operating margin | -6.2% | -6.2% | -11.0% |
| Date | Ticker | Company | Category | Trade Strategy | 6M Fwd Rtn | 12M Fwd Rtn | 12M Max DD |
|---|---|---|---|---|---|---|---|
| 11212025 | WU | Western Union | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | 7.5% | 7.5% | -0.4% |
| 11212025 | COIN | Coinbase Global | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | 15.2% | 15.2% | 0.0% |
| 11142025 | PYPL | PayPal | Dip Buy | DB | FCFY OPMDip Buy with High FCF Yield and High MarginBuying dips for companies with high FCF yield and meaningfully high operating margin | -2.5% | -2.5% | -7.5% |
| 11142025 | V | Visa | Monopoly | MY | Getting CheaperMonopoly-Like with P/S DeclineLarge cap with monopoly-like margins or cash flow generation and getting cheaper based on P/S multiple | -0.1% | -0.1% | -2.7% |
| 11072025 | WD | Walker & Dunlop | Dip Buy | DB | P/E OPMDip Buy with Low PE and High MarginBuying dips for companies with tame PE and meaningfully high operating margin | -6.2% | -6.2% | -11.0% |
Research & Analysis
Invest in Strategies
Wealth Management
Peer Comparisons for Tiptree
| Peers to compare with: |
Financials
| Median | |
|---|---|
| Name | |
| Mkt Price | 56.31 |
| Mkt Cap | 51.5 |
| Rev LTM | 32,712 |
| Op Inc LTM | - |
| FCF LTM | 3,924 |
| FCF 3Y Avg | 4,419 |
| CFO LTM | 3,924 |
| CFO 3Y Avg | 4,419 |
Growth & Margins
| Median | |
|---|---|
| Name | |
| Rev Chg LTM | 3.1% |
| Rev Chg 3Y Avg | 1.7% |
| Rev Chg Q | 0.6% |
| QoQ Delta Rev Chg LTM | 0.1% |
| Op Mgn LTM | - |
| Op Mgn 3Y Avg | - |
| QoQ Delta Op Mgn LTM | - |
| CFO/Rev LTM | 11.9% |
| CFO/Rev 3Y Avg | 18.2% |
| FCF/Rev LTM | 11.7% |
| FCF/Rev 3Y Avg | 18.2% |
Valuation
| Median | |
|---|---|
| Name | |
| Mkt Cap | 51.5 |
| P/S | 0.8 |
| P/EBIT | 7.6 |
| P/E | 14.2 |
| P/CFO | 3.7 |
| Total Yield | 10.5% |
| Dividend Yield | 3.4% |
| FCF Yield 3Y Avg | 22.8% |
| D/E | 0.4 |
| Net D/E | -1.1 |
Returns
| Median | |
|---|---|
| Name | |
| 1M Rtn | 2.5% |
| 3M Rtn | 2.7% |
| 6M Rtn | 7.2% |
| 12M Rtn | -7.0% |
| 3Y Rtn | 39.9% |
| 1M Excs Rtn | 2.5% |
| 3M Excs Rtn | -4.4% |
| 6M Excs Rtn | -7.5% |
| 12M Excs Rtn | -23.2% |
| 3Y Excs Rtn | -28.1% |
Returns Analyses
SEC Filings
Expand for More| Report Date | Filing Date | Filing |
|---|---|---|
| 9302025 | 10312025 | 10-Q 9/30/2025 |
| 6302025 | 7302025 | 10-Q 6/30/2025 |
| 3312025 | 4302025 | 10-Q 3/31/2025 |
| 12312024 | 3032025 | 10-K 12/31/2024 |
| 9302024 | 10302024 | 10-Q 9/30/2024 |
| 6302024 | 7312024 | 10-Q 6/30/2024 |
| 3312024 | 5012024 | 10-Q 3/31/2024 |
| 12312023 | 2292024 | 10-K 12/31/2023 |
| 9302023 | 11012023 | 10-Q 9/30/2023 |
| 6302023 | 8022023 | 10-Q 6/30/2023 |
| 3312023 | 5032023 | 10-Q 3/31/2023 |
| 12312022 | 3082023 | 10-K 12/31/2022 |
| 9302022 | 11022022 | 10-Q 9/30/2022 |
| 6302022 | 8082022 | 10-Q 6/30/2022 |
| 3312022 | 5052022 | 10-Q 3/31/2022 |
| 12312021 | 3142022 | 10-K 12/31/2021 |
Industry Resources
| Financials Resources |
| Federal Reserve Economic Data |
| Federal Reserve |
| FDIC Data |
| American Banker |
| The Banker |
| Banking Technology |
| Life & Health Insurance Resources |
| Insurance Business America |
| A.M. Best |
| National Underwriter |
| Insurance News |
External Quote Links
| Y Finance | Barrons |
| TradingView | Morningstar |
| SeekingAlpha | ValueLine |
| Motley Fool | Robinhood |
| CNBC | Etrade |
| MarketWatch | Unusual Whales |
| YCharts | Perplexity Finance |
| FinViz |